Dating for men at 50plus.

Remember what dating was like back in the 1980s? You went out with some mates, somebody caught your eye, you plucked up some courage went over and began a conversation. Maybe even asked for a dance if this was happening at a club. Eventually, the evening came to an end, you asked for a number and away you went.


Photos by Long Truong, John Arano and Quinn Al on Unsplash


Well, if you're 50plus and still dating you'll know that dating in 2020 is very different. The rules of the game have changed, we have changed.


The thought of searching for love can be daunting in this new digital age awash with a myriad of dating sites all professing to be the answer to our love dreams.

However, the one constant remains true out of all this and that being most women want the same as us men; to find a lifelong partner; to be a significant thought in the mind of the opposite sex.

Listed below are some tips and suggestions, gathered from around the 50plus4men's editing team, on dating at 50plus in 2020.


Photo by Sydney Rae on Unsplash

1. Confidence. At 50plus it's easy to feel too old, that your best years are behind you and to begin to question whether anyone is going to want you. Lynell Ross Health and wellness coach says "By the time people get to their 50s, they are usually not just older and wiser, but they are kinder, more forgiving, and more understanding. If you can be open to new possibilities, dating can actually be easier as you get older."

2. Out of practice. If it's been a while since you went on a date you can feel out of practice.

Nerves and anxiety can make dating seem daunting. It can be tempting to give up but as the old saying goes - if at first, you don't succeed try, try and try again. One bad date is just that. It's not a prophecy. By this point in our lives, we know that not everything works on our first attempt sometimes you just have to keep trying.


Photo by cottonbro from Pexels

3. Pressure. At 50plus it's very easy to feel that time is running out. It's only a short step from there to desperation. The pressure of desperation can take the fun out of dating. If you are feeling desperate take a breath, step back acknowledge the feeling but then recognise that you are not alone. Just as you are looking for the right person, that right person is out there looking for you. Take the pressure off yourself. Give yourself time. Remember if it's not fun don't do it.

4. Baggage. At 50 and over, almost anyone interesting has baggage (a word loaded with negativity) or just plain experience. Ex-wives, ex-husbands, children, divorce, debts i.e. commitments at 50plus. If you've lived at all you bring some if not all of these into whatever new relationships you form. Accept this fact, recognise that you will be bringing your own baggage to the party; be clear about what you want, and what you're willing to accept and then dive in. Honesty remains our most important tool.


It can be tempting to find common ground with a new date by discussing each other's past relationships but, bonding over your baggage is never a good way to start a new relationship. Stick to neutral ground and discuss other topics such as hobbies instead.


Photo by Will H McMahan on Unsplash

5. Compromise is harder than it used to be. When you're young, compromise is part of life it's part of growing up, by the time you're 50plus you're all grown up ( or should be), you have set patterns of behaviour, feelings about life, values, goals, and this can make a compromise to accommodate someone else needs can be much more difficult. If you've been in any kind of relationship then you'll know that compromise is part of the game. So if you're dating at 50plus remember sometimes the old dog needs to learn new tricks if he wants to have that new person in his life.


6. Fewer single friends. It seems to be a fact of life that at 50plus most of us have fewer friends than we did when we were younger. At 50plus most of us have a few close friends as opposed to the truckload of acquaintances of our youth. And most of those friends that we do have aren't single, they are married or in a long term relationship. The pool of potential single people around has been significantly reduced, but they are still out there. Use your social network. I dismissed a friend of mine's matchmaking ideas for a mutual acquaintance, only to discover after she had put the two of them together that sparks had flown. You never know where that next right person might be.

Photo by Christin Hume on Unsplash


7. Your sexual health is different.

Every individual is unique, of course. But as a group, men who are 50plus are likely contending with a different sort of sexual health profile than we did when we were younger. See our blog posts on:

  • Sex after prostate surgery

  • An enlarged prostate at 50plus

We may suffer from less vigour, inconsistent erections which are interrupted more easily, or find that we are simply more nervous than we were before. The key, as is often the way in life, is honesty. Take the pressure off yourself, talk to your new partner about how you're feeling. Most people will have faced their own issues as they have grown older. You may be pleasantly surprised by how understanding your new partner can be.

8. The dread of technology. When I got divorced in my late 40's a friend of mine asked whether I was going to try internet dating. My answer was " last time I was free there wasn't even an Internet, let alone an Internet dating site." Of course, I knew what they were, but I'd never used one. I was stumped. I didn't know what to do, or even how to approach online dating. So I asked a friend of mine, who had been online dating for a while. Here are some of the suggestions he came up with (remember these are suggestions and not rules):

  • The first step is to make the commitment to yourself that the Internet will be your main source in the pursuit of your new lover.

Picture: The next step is to acquire a few decent and current photos. I suggest you find a local professional photographer. Inform them that your photos are primarily for Internet dating and they should be able to do the rest. Ensure, you are smiling and you are facing the camera. You might want to take a few changes of clothing. The picture is the most important element of your Internet profile and so it would be ideal spending time to get this right.

  • Profile: The next thing you have to do is write a few key sentences about yourself. You may be lost for words and so the simple solution is to search the internet for good examples of an internet profile you can cut and paste and use this as a guide for your own profile.

  • You now have your photo and profile, the next thing you need to do is to decide which Internet site you want to use. There are a plethora of sites, the key to choosing one is to find those that are free to send and receive messages or charge a minimal price to send and receive messages. Plenty of Fish, Plenty More Fish and Match are good examples. Plenty of Fish is completely free.

  • Your next step is to start contacting the woman. “Hey there”, yes just these two words “Hey there”. Send this short message to women who you are attracted to.

  • Be persistent, consistent and patient, you will eventually receive a reply normally in the form of “Hi” or “Hey”.

  • You can then reply with “How are you? “ or “How is your day going?”. The key point here is to keep the length of your messages to be fairly similar in length to the messages you receive from the woman.

  • Continue exchanging messages with the woman; try to incorporate in your reply a reference to the contents of the message you receive and also keep you reply witty and with an ending that encourages a reply.

  • After you have exchanged messages for a week or so, you can ask for her number. The key here is to ask “Would you like to exchange mobile numbers”. Asking in the manner shows you are being polite and not presumptuous.


  • You can now communicate via text or Whatsapp and the nature of the texts can now start becoming more personal e.g. you can start wishing her “good morning” and “good night”.

  • Now ask her “would you like to chat on the phone”. Agree a time, make that call. On the first call agree boundaries i.e. what is the latest time you can call her, or should you send text prior to making a call. The key point here is not to make any assumptions about her preferences and it shows you are being thoughtful and considerate. After a few calls and when it feels right to ask for a date

Key Points

- Get a recent and decent photo

- Search the Internet for examples of Internet profiles

- Keep the initial message brief .e.g. “Hey there”

- Keep the length of your messages similar in length to those you receive.

- When asking for her number always say “Would you like to exchange numbers?” rather “Can I have your number?”.

- Agree a time to call and on the first call agree on boundaries i.e. when to call and how late can you call.

Well dating at 50plus can be a challenge, but if you want somebody in your life and you don't have anyone at the moment, then at 50plus we encourage you to meet that challenge head-on. We hope the ideas, suggestions and comments made here help you to find that someone special. Good luck


Author JG & an anonymous friend.


73 views0 comments